Chat Roulette

This happened last night. Sorry if it's a little long, but I wanted to get it right.

Insomnia sucks. By the time two am approached, it was obvious I wasn't going to fall asleep any time soon, so I decided to go online. It was too much effort to get dressed again, so I wrapped a blanket around my shoulders and over my head like a hood, and headed downstairs to my macbook.

My latest internet obsession is a site called chatroulette. For those who are not familiar, its a site that allows you to have chat and cam conversations with random strangers. A large chunk of the people on there are guys asking to see boobs, or guys masturbating, and there are a lot of boring ones that just sit there looking blank...but there are quite a few entertaining ones as well. Funny costumes or activities. Occasionally you can even happen upon a good conversation.

The first couple of people that came up clicked off fairly quickly, but the third was a guy around my age, shirtless, visible from the shoulders up, sitting on a bed. Rather than clicking off right away, he said 'Hi.' I said 'Hi' back.

He noticed the blanket and asked if I was cold. 'Freezing!' I replied, and he laughed, responding that his bedroom was actually pretty warm. He asked my age and where I was from, and when I told him 20 from Canada, he said 'No wonder you're so cold!' and we both laughed. He told me he was 19, and then his face changed a little, becoming a little too casual, and he asked 'So...gay or straight?'

Now, I'm straight, but I've always been a bit curious about other guys, and right then I was horny as hell and beginning to see that this might lead to some safe, long-distance fun. So I said 'I'm bi, actually. But that's ok, because my girlfriend is too. We have some great parties.'

He laughed and said 'I bet!' He asked how long I'd been bi, and I said since high school. He told me he was straight until he got to college, and that since then he'd been sort of bi-curious. I asked if he'd ever acted on that curiosity, and he said 'I gave and received a hand job once.' Then he asked if I'd had a lot of bi experiences, and I said 'Not a lot. But I've done the 'Devils 3-Way' with my girlfriend and a buddy.'

'So no gay sex then?'

'Well, no penetration...that's strictly for girls,' I said with a laugh. 'But I've done some other stuff.'

He got quiet for a minute, and then with a bit of a nervous smile, asked 'So...do you ever get freaky on here?'

'Define freaky.'

'Well...' Nervous laugh. 'You ever get naked?'

I smiled. 'I'm naked under the blanket.'

'Really? I'm in boxers, lol' he typed, and I said that was cool. Then he asked if I would show him.

'You first!' I laughed, and he sighed.

'Of course,' he said, and shifted position, moving his laptop so the cam was aimed at his crotch. Then he pulled down the front of his boxers and took out his semi-hard cock and balls, giving them a squeeze. Its kind of hard to judge size on a webcam, but it was a nice one and I told him so.

The cam returned to his face and he smiled. 'Your turn.' I turned my macbook around and showed him my dick, which was a little past half mast.

'That looks pretty big dude,' he said, and I thanked him. He asked how big it actually was, and I told him 6 1/2 inches, 'But on a good day, I can push 7.'

He said on his best days, he could hit 8, and I told him that was awesome. 'I've had no complaints,' he said, and we both laughed.

We continued chatting for a bit, talking about sex. I asked if he'd ever considered going further than the hand jobs he'd done, and he said 'Probably, if the opportunity presented itself.'

I continued gently rubbing my dick, out of frame, and he was obviously still playing with himself because the cam kept jiggling. Then he laughed and said 'I'm trying to jack off, but my laptop keeps getting in the way!' He moved the cam again, showing his now fully-erect penis, then moved it back to his face. 'Let's see that 7-incher again,' he said, so I showed him my hard-on.

Then he asked if I wanted to have a jack-off race, and I said 'Sure, why not?' I moved my macbook onto the foot rest of my recliner, so my junk was fully displayed, while he set his laptop on the bed, pulled off his boxers, and laid on his side. We did a countdown, and then each grabbed our cocks and started pumping.

My friend changed positions a few times as he went, apparently both for comfort and to show off better. I felt my orgasm approach quickly as I jacked my dick and rubbed my balls, and held off a bit because I was a bit embarrassed to be going so fast...stupid, since it was a race and all, haha. Probably 30 seconds later, he shot his wad, four quick spurts onto his belly, so I went for broke as he sat up and wiped his hands. As I hit the point of no-return, he typed 'I win!' and clicked Next, and I blew my load just as the startled face of the next user popped up on my screen.

It was a little disappointing...he was a cool guy, and I would have liked to add him as a regular online buddy...but it was still a fun experience, and definitely one I wouldn't mind repeating. (who knows...maybe he reads this site? haha)